Phenyl azo cyanothienyl azo anilino dyestuffs

ABSTRACT

Disazo dyestuffs for polyester fibers represented by the following general formula: ##STR1## wherein X represents a hydrogen atom, a chlorine atom, a trifluoromethyl group or a nitro group, Y represents a cyano group, a lower alkoxycarbonyl group or a lower alkoxyalkoxycarbonyl group, Z represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or an acylamino group, R 1  represents a hydrogen atom, a lower alkyl group, a cyanoalkyl group, a hydroxyalkyl group, a lower alkoxyalkyl group, a lower alkoxyalkoxyalkyl group, an aryloxyalkyl group, an acyloxyalkyl group, an alkenyloxyalkyl group, a lower alkoxycarbonylalkyl group, a lower alkoxyalkoxycarbonylalkyl group, a lower alkoxycarbonyloxyalkyl group, an alkenyl group or an aralkyl group, R 2  represents a hydrogen atom, a hydroxyalkyl group, a lower alkoxyalkyl group, a lower alkoxyalkoxyalkyl group, an aryloxyalkyl group, an acyloxyalkyl group, an alkenyloxyalkyl group, a lower alkoxycarbonylalkyl group, a lower alkoxyalkoxycarbonylalkyl group, a lower alkoxycarbonyloxyalkyl group, an alkenyl group or an aralkyl group, and R 3  represents a hydrogen atom, a methyl group, a chlorine atom or a methoxy group, but R 2  may represent a lower alkyl group in case that Y represents a lower alkoxycarbonyl group, Z represents an acylamino group or R 3  represents a methyl group. The dyestuffs dye polyester fibers in a brilliant reddish-blue or blue shade and have good fastness properties, excellent temperature stability and pH stability in dyeing.

FIELD OF THE INVENTION

The present invention relates to disazo dyestuffs for polyester fibers.

The dyestuffs of the present invention dye polyester fibers in brilliant reddish blue or blue shade and have good fastness properties, especially good fastness to light, good fastness to sublimation and good fastness to water and excellent temperature stability and pH stability in dyeing.

Further, the dyestuffs of the present invention less cause pollution of white texture in printing and have excellent white dischargeability in alkali resist- or discharge printing.

BACKGROUND OF THE INVENTION

The following dyestuff has been described in Japanese Patent Application (OPI) No. 47680/74 (U.S. Pat. No. 4,264,495) (the term "OPI" as used herein refers to a "published unexamined Japanese patent application"): ##STR2## The above-described dyestuff causes pollution of white texture in printing and has insufficient white discharge-ability in alkali resist- or discharge printing.

Dyestuffs represented by the following general formula have been described in Japanese Patent Application (OPI) No. 41734/76 (German Patent Application (OLS) No. 2,438,496). ##STR3## wherein K represents a group of coupling components, R₁ represents C₁ -C₄ alkyl, aryl, C₁ -C₄ alkoxycarbonyl or hydrogen, R₂ represents aryl, C₁ -C₄ alkoxycarbonyl, CONW₁ W₂ or cyano, X₁ and X₂ represent each hydrogen, chlorine, bromine, cyano, CF₃, nitro, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, phenyl, C₁ -C₄ alkycarbonyl, C₁ -C₄ alkoxycarbonyl, C₁ -C₄ alkylsulfonyl, arylsulfonyl, benzylsulfonyl, COOH, SO₂ W₁ W₂ or CONW₁ W₂ but do not represent hydrogen at the same time, X₃ represents hydrogen, C₁ -C₄ alkyl, C₁ -C₄ alkoxy, chlorine, bromine or cyano, and X₄ represents hydrogen, methyl, chlorine or bromine, wherein W₁ and W₂ represent each H, C₁ -C₄ alkyl or hydroxyethyl or form a residue of a 5-member or 6-member saturated heterocyclic ring by linking together. However, dyestuffs described in concrete in the above-described Japanese Patent Application (OPI) No. 41734/76 have a problem for practical use because of having inferior temperature stability in dyeing.

SUMMARY OF THE INVENTION

The disazo dyestuffs of the present invention are represented by the following general formula (I): ##STR4## wherein X represents a hydrogen atom, a chlorine atom, a trifluoromethyl group or a nitro group, Y represents a cyano group, a lower alkoxycarbonyl group or a lower alkoxyalkoxycarbonyl group, Z represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or an acylamino group, R¹ represents a hydrogen atom, a lower alkyl group, a cyanoalkyl group, a hydroxyalkyl group, a lower alkoxyalkyl group, a lower alkoxyalkoxyalkyl group, an aryloxyalkyl group, an acyloxyalkyl group, an alkenyloxyalkyl group, a lower alkoxycarbonylalkyl group, a lower alkoxyalkoxycarbonylalkyl group, a lower alkoxycarbonyloxyalkyl group, an alkenyl group or an aralkyl group, R² represents a hydrogen atom, a hydroxyalkyl group, a lower alkoxyalkyl group, a lower alkoxyalkoxyalkyl group, an aryloxyalkyl group, an acyloxyalkyl group, an alkenyloxyalkyl group, a lower alkoxycarbonylalkyl group, a lower alkoxyalkoxycarbonylalkyl group, a lower alkoxycarbonyloxyalkyl group, an alkenyl group or an aralkyl group, and R³ represents a hydrogen atom, a methyl group, a chlorine atom or a methoxy group, but R² may represent a lower alkyl group in case that Y represents a lower alkoxycarbonyl group, Z represents an acylamino group or R³ represents a methyl group.

DETAILED DESCRIPTION OF THE INVENTION

In the above-described general formula (I), examples of the lower alkoxycarbonyl group represented by Y include a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group, etc.; and examples of the lower alkoxyalkoxycarbonyl group include a methoxyethoxycarbonyl group, an ethoxyethoxycarbonyl group, a propoxyethoxycarbonyl group and a butoxyethoxycarbonyl group, etc.

Examples of the acylamino group represented by Z include an acetylamino group, a chloroacetylamino group, a propionylamino group, a methylsulfonylamino group, a chloropropionylamino group, a methoxycarbonylamino group and an ethoxycarbonylamino group, etc.

Examples of the lower alkyl group represented by R¹ include a methyl group, an ethyl group and straight chain or branched chain propyl and butyl groups, etc.; and examples of the cyanoalkyl group include a cyanomethyl group and a cyanoethyl group, etc.

Examples of hydroxyalkyl groups represented by R¹ and R² include a hydroxyethyl group, a hydroxypropyl group, a hydroxybutyl group and a hydroxyhexyl group, etc.; examples of lower alkoxyalkyl groups include a methoxyethyl group, an ethoxyethyl group and a butoxyethyl group, etc.; examples of lower alkoxyalkoxyalkyl groups include a methoxyethoxyethyl group and an ethoxyethoxyethyl group, etc.; an example of aryloxyalkyl groups include a phenoxyethyl group, etc.; examples of acyloxyalkyl groups include an acetyloxyethyl group, a propionyloxyethyl group and a benzoyloxyethyl group, etc.; examples of alkenyloxyalkyl groups include an allyloxyethyl group and a crotyloxyethyl group, etc.; examples of the lower alkoxycarbonylalkyl groups include a methoxycarbonylmethyl group, a methoxycarbonylethyl group, a methoxycarbonylpropyl group, an ethoxycarbonylmethyl group, an ethoxycarbonylethyl group and a butoxycarbonylethyl group, etc.; examples of the lower alkoxyalkoxycarbonylalkyl groups include a methoxyethoxycarbonylmethyl group, a methoxyethoxycarbonylethyl group, an ethoxyethoxycarbonylethyl group, a methoxyethoxycarbonylpropyl group and a butoxyethoxycarbonylethyl group, etc.; examples of the lower alkoxycarbonyloxyalkyl groups include a methoxycarbonyloxyethyl group and an ethoxycarbonyloxyethyl group, etc.; examples of the alkenyl groups include an allyl group, a 2-methylallyl group and a crotyl group, etc.; and examples of the aralkyl groups include a benzyl group and a phenethyl group, etc.

The disazo dyestuffs represented by the general formula (I) can be prepared by a process which comprises diazotizing amines represented by the following formula (II): ##STR5## wherein X represents the same meaning as described above, coupling the diazotized amines with aminothiophenes represented by the following formula (III): ##STR6## wherein Y represents the same meaning as described above, diazotizing the resulted monoazo compounds represented by the following formula (IV): ##STR7## wherein X and Y represent each the same meaning as described above, and coupling the diazotized monoazo compounds with anilines represented by the following formula (V): ##STR8## wherein Z, R¹, R² and R³ represent each the same meaning as described above.

Examples of fibers capable of dyeing with using the disazo dyestuffs of the present invention include polyethylene terephthalate fibers, polyester fibers composed of polycondensates of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane, and blended spinning goods and woven cloth of blended spun yarns prepared with using natural fibers such as cotton, silk, or wool, etc., and the above-described polyester fibers.

In order to dye the polyester fibers with using the dyestuffs represented by the above-described general formula (I) of the present invention, a dyeing bath or a printing paste is prepared by dispersing the dyestuff in an aqueous medium with using a dispersing agent such as a condensate of naphthalenesulfonic acid and formaldehyde, higher alcohol sulfate or higher alkylbenzenesulfonic acid salt, etc., by means of a conventional method, because the dyestuff is insoluble or bad-soluble in water, and dip-dyeing or printing is carried out. For example, in case of dip-dyeing, dyeings having excellent fastness can be obtained on the polyester fibers or blended spinning goods thereof, when a conventional dyeing process such as a high-temperature dyeing process, a carrier dyeing process or a thermosol dyeing process, etc., is used. In such a case, if necessary, further excellent results are obtained by adding an acid substance such as formic acid, acetic acid, phosphoric acid or ammonium sulfate, etc., to the dyeing bath.

Further, the dyestuffs represented by the above-described general formula (I) of the present invention may be used together with the same kind of dyestuff or with another kind of dyestuff. In such cases, good results, for example, an improvement of dyeing properties, etc., are obtained sometimes by blending two or more dyestuffs represented by the above-described general formula (I).

As resist- or discharge printing process for polyester fibers used in the present invention, there are various processes. The first process comprises carrying out pad-dyeing woven cloth of polyester fibers with a dispersion containing monoazo dyestuffs represented by the general formula (I) and various auxiliaries, drying at a temperature ranging from 80° C. to 150° C., printing the resulted cloth with a resist- and discharge printing paste containing bases such as K₂ CO₃ and various dyeing auxiliaries, subjecting thereafter a heat treatment at a temperature ranging from 100° C. to 230° C. to set the monoazo dyestuffs represented by the general formula (I) and decompose the monoazo dyestuffs on the area where the resist- and discharge printing paste was not applied, and carrying out a post-treatment by a conventional manner. The second process comprises printing woven cloth of polyester fibers with a resist- and discharge printing paste, drying or not drying at a temperature ranging from 80° C. to 150° C., subsequently printing the woven cloth with a printing paste containing the monoazo dyestuffs represented by the general formula (I) and various dyeing auxiliaries, subjecting thereafter a heat treatment at a temperature ranging from 100° C. to 230° C. to set the monoazo dyestuffs represented by the general formula (I) and decompose the monoazo dyestuffs on the area where the resist- and discharge printing paste was not applied, and carrying out a post-treatment by a conventional manner. Further, the third process comprises printing woven cloth of polyester fibers with the monoazo dyestuffs represented by the general formula (I) and various auxiliaries, drying at a temperature ranging from 80° C. to 150° C., printing the woven cloth with a resist- and discharge printing paste, subjecting a heat treatment at a temperature ranging from 100° C. to 230° C. to set the monoazo dyestuffs represented by the general formula (I) and decompose the monoazo dyestuffs on the area where the resist- and discharge printing paste was applied, and carrying out a post-treatment by a conventional manner.

When the above-described various resist- and discharge printing processes are applied to the woven cloth of polyester fibers, it is possible to form multicolor designs by addition of alkali resisting dyestuffs described in the following to the resist- and discharge printing paste.

In the following, the present invention is illustrated in concrete with reference to examples.

EXAMPLE 1 ##STR9##

100 g of polyester fibers was dipped in a dyeing bath prepared by dispersing 0.5 g of a dyestuff represented by the above-described formula in 3 l of water containing 1 g of naphthalenesulfonic acid-formaldehyde condensate and 2 g of higher alcohol sulfate. After the fibers were dyed at 130° C. for 60 minutes, they were subjected to soaping, washing and drying, by which dyed fibers having a brilliant reddish blue shade were obtained. The resulted dyed fibers had good fastness to light, good fastness to sublimation and good fastness to water, and the above-described dyestuff had good temperature stability and good pH stability in dyeing.

The dyestuff used in this example was prepared as follows.

9.3 g of aniline was dissolved in 100 ml of 7% hydrochloric acid. After the resulted solution was cooled to 2° C., 50 ml of 2N sodium nitrite were added thereto. The temperature in this case was controlled so as not to exceed 5° C. The resulted solution of diazonium salt of aniline was added to a solution containing 12.4 g of 2-amino-3-cyanothiophene in 200 ml of methanol at 2° C., and the mixture was stirred for 2 hours at this temperature. After the separated monoazo compound was separated by filtration, it was washed with water and dried. 11.4 g of this monoazo compound (2-amino-3-cyano-5-phenylazothiophene) was added to a mixture composed of 114 ml of acetic acid and 114 ml of phosphoric acid. Then, nitrosylsulfuric acid (which was prepared by dissolving 3.5 g of sodium nitrite in 20 g of 97% sulfuric acid) was slowly added to the resulted mixture, and the mixture was stirred at the same temperature as described above for 30 minutes to prepare a solution of diazotized monoazo compound.

9.3 g of N-allyl-N-(β-cyanoethyl)aniline was dissolved in 200 ml of methanol, and the resulted solution was added to a mixture composed of 200 g of ice and 100 ml of water. To the resulted mixture, the previously prepared solution of diazotized monoazo compound was added, and the resulted mixture was stirred at 0° to 5° C. for 2 hours. After the separated disazo dyestuff was separated by filtration, it was washed with water and dried. The resulted dyestuff had λmax (acetone) of 612 nm.

EXAMPLE 2 ##STR10##

A woven fabric of polyester fibers was printed with using a printing paste which was prepared by finely dispersing 30 g of a dyestuff represented by the above-described structural formula and adding 24 g of Cellucol PBL-600 (produced by Adachi Koryo Co.), 45.5 g of Kiprogum P-20N (produced by Nichiden Chemical Co.), 1.5 g of tartaric acid, 10.2 g of MS Powder (produced by Meisei Kagaku Co.), 30 g of Meiprinter Y-75 (produced by Meisei Kagaku Co.) and 858.8 ml of water. It was subjected to setting at 175° C. for 6 minutes by superheated steam, a reductive post-treatment and a soaping treatment. After carried out rinsing and drying, a dyed woven fabric having a brilliant blue shade of especially good fastness to light, sublimation and water was obtained. The temperature stability and the pH stability of the above-described dyestuff in dyeing were excellent.

The dyestuff used in this example was prepared according to Example 1. This dyestuff had λmax (acetone) of 610 nm.

EXAMPLE 3

A woven fabric of polyester fibers was printed with using a resist- and discharge printing paste composed of 60 g of sodium carbonate, 60 g of Color Fine AD (produced by Dai-ichi Kogyo Seiyaku Co.), 600 g of a 25% aqueous solution of Texprint LB (produced by Grunau Co.) and 280 ml of water, and dried at 80° to 100° C. After dried, it was overprinted with using a printing paste which was prepared by finely dispersing 30 g of a dyestuff represented by the following structural formula ##STR11## and adding 24 g of Cellucol PBL-600 (produced by Adachi Koryo Co.), 45.5 g of Kiprogum P-20N (produced by Nichiden Chemical Co.), 1.5 g of tartaric acid, 10.2 g of MS Powder (produced by Meisei Kagaku Co.), 30 g of Meiprinter Y-75 (produced by Meisei Kagaku Co.) and 858.8 ml of water. It was subjected to setting at 175° C. for 6 minutes by superheated steam, a reductive post-treatment and a soaping treatment. After carrying out rinsing and drying, a dyed woven fabric having a brilliant blue shade of especially good fastness to light, sublimation and water was obtained. A very excellent white resist printing having a sharp outline was obtained on the area where the sodium carbonate containing resist- and discharge printing paste was applied by printing. The temperature stability and the pH stability of the above-described dye in dyeing were excellent.

The dyestuff used in this example was prepared according to Example 1. This dyestuff had λmax (acetone)of 619 nm.

EXAMPLE 4

Dyestuffs shown in the following Table 1 and Table 2 were prepared by the same process as in Example 1. Polyester fibers were dyed with using these dyestuffs. λmax (acetone) of each dyestuff and the shade of dyeing fabrics are shown in these tables.

                                      TABLE 1                                      __________________________________________________________________________      ##STR12##                                                                                                                                λ max                                                                   (ace-                                                               Dyeing Shade                                                                              tone)               No.                                                                               X  Y         Z       R.sup.1     R.sup.2     (on polyester                                                                             nmbers)             __________________________________________________________________________     1  H  COOCH.sub.3                                                                              H       C.sub.2 H.sub.4 CN                                                                         CH.sub.2CHCH.sub.2                                                                         Brilliant reddish                                                                         582e                2  "  CN        NHCOCH.sub.3                                                                           CH.sub.2CHCH.sub.2                                                                         "           Brilliant                                                                                 631e                3  "  "         CH.sub.3                                                                               C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.4 OCH.sub.2 CHCH.sub.2                                                       "          604                 4  "  "         H       "           CH.sub.2CHCH.sub.2                                                                         "          597                 5  "  "         "       CH.sub.2CHCH.sub.2                                                                         CH.sub.2 COOCH.sub.3                                                                       Reddish                                                                                   595e                6  "  "         "       "           C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                        Brilliant                                                                                 608e                7  "  "         "       "           C.sub.2 H.sub.4 OCH.sub.3                                                                  "          618                 8  "  COOCH.sub.3                                                                              "       "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                Reddish                                                                                   593e                9  "  COOC.sub.2 H.sub.5                                                                       "       "           "           "          592                 10 "  CN        CH.sub.3                                                                               "           "           Brilliant                                                                                 620e                11 "  "         "       C.sub.2 H.sub.4 CN                                                                         CH.sub.2CHCH.sub.2                                                                         "          607                 12 "  "         "       CH.sub.2 CN "           "          597                 13 "  COOCH.sub.3                                                                              "       C.sub.2 H.sub.4 CN                                                                         "           Reddish                                                                                   592e                14 "  "         "       "           C.sub.2 H.sub.4 OCH.sub.2CHCH.sub.2                                                        "          590                 15 "  CN        NHCOCH.sub.3                                                                           "           CH.sub.2CHCH.sub.2                                                                         Brilliant                                                                                 625e                16 "  "         "       C.sub.2 H.sub.4 OCH.sub.2CHCH.sub.2                                                        C.sub.2 H.sub.4 OCH.sub.2 CHCH.sub.2                                                       "          630                 17 "  "         H       C.sub.2 H.sub.4 CN                                                                         CH.sub.2C(CH.sub.3)CH.sub.2                                                                Reddish                                                                                   598e                18 "  "         "       CH.sub.2CHCH.sub.2                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                  Brilliant                                                                                 620e                19 "  COOCH.sub.3                                                                              "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            Brilliant reddish                                                                         585e                20 "  "         "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                                Brilliant                                                                                 600e                21 "  COOC.sub.2 H.sub.5                                                                       "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            Brilliant reddish                                                                         585e                22 "  COOCH.sub.3                                                                              CH.sub.3                                                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OH                                                                         Brilliant                                                                                 625e                23 "  "         NHCOCH.sub.3                                                                           "           C.sub.2 H.sub.5                                                                            "          620                 24 "  "         H       "           C.sub.2 H.sub.4 OCH.sub.3                                                                  Brilliant reddish                                                                         595e                25 "  "         "       "           C.sub.2 H.sub.4 COOCH.sub.3                                                                Reddish                                                                                   600e                26 "  "         "       "           CH.sub.2 COOCH.sub.3                                                                       "          582                 27 "  "         "       "           C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                        "          596                 28 "  "         "       "           C.sub.2 H.sub.4 OC.sub.4 H.sub.9                                                           Blue       606                 29 "  COOC.sub.2 H.sub.5                                                                       "       "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                Reddish                                                                                   593e                30 "  COOCH.sub.3                                                                              "       "           C.sub.2 H.sub.5                                                                            Blue       615                 31 "  "         "       CH.sub.3    CH.sub.3    "          608                 32 "  "         "       C.sub.2 H.sub.5                                                                             ##STR13##  "          603                 33 "  "         "       "           H           Reddish                                                                                   580e                34 "  "         "       "                                                                                           ##STR14##  Blue       605                 35 "  "         "       C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          600                 36 "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                Reddish                                                                                   583e                37 "  "         "       C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                "          585                 38 "  "         CH.sub.3                                                                               C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            "          596                 39 "  "         "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                                Blue       604                 40 "  COOC.sub.4 H.sub.9 (n)                                                                   "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            Reddish                                                                                   596e                41 "  COOCH.sub.3                                                                              Cl      C.sub.2 H.sub.5                                                                            H           "          590                 42 "  "         "       C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                "          595                 43 "  "         "       C.sub.2 H.sub.4 OCOOCH.sub.3                                                               C.sub.2 H.sub.4 OCOOCH.sub.3                                                               "          592                 44 "  "         NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            Blue       630                 45 "  "         NHCOC.sub.2 H.sub.5                                                                    C.sub.2 H.sub.4 CN                                                                         "           "          610                 46 "  "         NHCOC.sub.2 H.sub.4 Cl                                                                 C.sub.2 H.sub.5                                                                            "           "          628                 47 "  "         NHSO.sub.2 CH.sub.3                                                                    "           "           "          624                 48 "  "         NHCOOCH.sub.3                                                                          "           "           "          628                 49 "  "         NHCOCH.sub.3                                                                           C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          640                 50 "  "         "       C.sub.2 H.sub.4 OH                                                                         C.sub.2 H.sub.4 OH                                                                         "          646                 51 "  "         "       C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                "          618                 52 "  CN        H       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                                Brilliant                                                                                 618e                53 "  "         "       "           CH.sub.2 COOCH.sub.3                                                                       Brilliant reddish                                                                         597e                54 "  "         CH.sub.3                                                                               C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                Brilliant                                                                                 615e                55 "  "         "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OH                                                                         "          648                 56 "  "         NHCOCH.sub.3                                                                           "           C.sub.2 H.sub.5                                                                            "          645                 57 "  "         H       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          604                 58 "  "         "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 COOC.sub.2 H.sub.4                                             OCH.sub.3   "          620                 59 "  "         "       "           C.sub.2 H.sub.4 OCOOCH.sub.3                                                               "          617                 60 "  "         "       C.sub.4 H.sub.9 (n)                                                                        H           "          626                 61 "  "         "       C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                Reddish                                                                                   602e                62 "  "         "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OH                                                                         Brilliant                                                                                 638e                63 "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                "          604                 64 "  "         "       C.sub.2 H.sub.5                                                                             ##STR15##  "          628                 65 "  "         "       "                                                                                           ##STR16##  "          620                 66 "  "         "       "           C.sub.2 H.sub.4 OCH.sub.3                                                                  "          631                 67 "  "         "       "           C.sub.2 H.sub.4 OC.sub.2 H.sub.4                                               OCH.sub.3   "          630                 68 "  "         CH.sub.3                                                                               "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          631                 69 "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                "           "          613                 70 "  "         "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 COOCH.sub.3                                                                "          628                 71 "  "         "       C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          638                 72 "  "         "       C.sub.2 H.sub.4 OCOOCH.sub.3                                                               C.sub.2 H.sub.4 OCOOCH.sub.3                                                               "          617                 73 "  "         Cl      H           C.sub.2 H.sub.4 COOCH.sub.3                                                                "          608                 74 "  "         "       C.sub.2 H.sub.5                                                                            H           "          625                 75 "  "         "       C.sub.2 H.sub.4 OH                                                                         C.sub.2 H.sub.4 OH                                                                         "          633                 76 "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          610                 77 "  "         NHCOCH.sub.3                                                                           "           "           "          625                 78 "  "         "       C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          635                 79 "  "         "       H           C.sub.2 H.sub.4 COOC.sub.2 H.sub.4                                             OCH.sub.3   "          615                 80 "  "         NHSO.sub.2 CH.sub.3                                                                    C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            "          638                 81 "  "         NHCOOCH.sub.3                                                                          "           "           "          640                 82 "  "         NHCOC.sub.2 H.sub.4 Cl                                                                 "           "           "          640                 83 "  "         Br      "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                Blue       602                 84 "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                "           Violet     587                 85 "  "         "       C.sub.2 H.sub.4 OCH.sub.3                                                                  CH.sub.2 COOCH.sub.3                                                                       "          588                 86 "  COOC.sub.2 H.sub.4 OCH.sub.3                                                             H       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          593                 87 "  COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                      "       C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          596                 88 "  "         "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.4 OCOOCH.sub.3                                                               "          581                 89 Cl COOCH.sub.3                                                                              "       "           C.sub.2 H.sub.5                                                                            Reddish                                                                                   602e                90 "  "         "       C.sub.2 H.sub.5                                                                            "           Brilliant                                                                                 638e                91 "  "         "       "                                                                                           ##STR17##  "          630                 92 "  COOC.sub.2 H.sub.5                                                                       "       CH.sub.3    C.sub.2 H.sub.4 COOCH.sub.3                                                                Reddish                                                                                   598e                93 "  CN        Br      CH.sub.2CHCH.sub.2                                                                         "           Blue       597                 94 "  "         H       C.sub.2 H.sub.4 CN                                                                         CH.sub.2CHCH.sub.2                                                                         Brilliant                                                                                 602e                95 "  "         "       CH.sub.2 COOCH.sub.3                                                                       "           "          600                 96 "  "         CH.sub.3                                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                                "           "          612                 97 "  "         H       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          626                 98 "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          613                 99 "  "         CH.sub.3                                                                               C.sub.2 H.sub.5                                                                             ##STR18##  "          650                 100                                                                               "  "         NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            "          645                 101                                                                               CF.sub.3                                                                          COOCH.sub.3                                                                              H       C.sub.2 H.sub.4 CN                                                                         CH.sub.2CHCH.sub.2                                                                         Reddish                                                                                   599e                102                                                                               "  "         CH.sub.3                                                                               "           "           Brilliant                                                                                 610e                103                                                                               "  CN        H       "           "           "          604                 104                                                                               "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                "           "          615                 105                                                                               "  "         "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.4 OCH.sub.2CHCH.sub.2                                                        "          613                 106                                                                               "  "         NHCOCH.sub.3                                                                           "           CH.sub.2CHCH.sub.2                                                                         "          642                 107                                                                               "  "         CH.sub.3                                                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OH                                                                         "          656                 108                                                                               "  "         NHCOCH.sub.3                                                                           "           C.sub.2 H.sub.5                                                                            "          650                 109                                                                               "  COOCH.sub.3                                                                              H       "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                Brilliant reddish                                                                         605e                110                                                                               "  CN        "       "           C.sub.2 H.sub.4 COOC.sub.2 H.sub.4                                             OCH.sub.3   Brilliant                                                                                 632e                111                                                                               "  "         "       "           C.sub.2 H.sub.4 OCH.sub.3                                                                  "          636                 112                                                                               "  COOCH.sub.3                                                                              NHCOCH.sub.3                                                                           "           C.sub.2 H.sub.5                                                                            "          636                 113                                                                               "  CN        "       "           "           "          650                 114                                                                               "  "         CH.sub.3                                                                               "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          642                 115                                                                               "  "         "       "           C.sub.2 H.sub.4 COOCH.sub.3                                                                "          643                 116                                                                               "  "         "       C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                "          628                 117                                                                               "  "         NHCOCH.sub.3                                                                           C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          644                 118                                                                               "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          636                 119                                                                               "  COOCH.sub.3                                                                              CH.sub.3                                                                               C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            "          616                 120                                                                               "  "         "       C.sub. 2 H.sub.5                                                                           C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          629                 121                                                                               "  COOC.sub.2 H.sub.5                                                                       Cl      "           "           "          620                 122                                                                               "  COOC.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                      Br      C.sub.2 H.sub.4 OCOCH.sub.3                                                                "           Blue       593                 123                                                                               "  COOC.sub.2 H.sub.4 OC.sub.4 H.sub.9 (n)                                                  CH.sub.3                                                                               C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 OCH.sub.3                                                                  "          605                 124                                                                               NO.sub.2                                                                          CN        H       "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                Brilliant                                                                                 638e                125                                                                               "  COOCH.sub.3                                                                              "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            Brilliant reddish                                                                         608e                126                                                                               "  CN        "       C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.4 COOCH.sub.3                                                                Brilliant                                                                                 639e                127                                                                               "  "         "       "           C.sub.2 H.sub.4 OCOOCH.sub.3                                                               "          636                 128                                                                               "  "         "       C.sub.4 H.sub.9 (n)                                                                        H           "          629                 129                                                                               "  "         "       C.sub.2 H.sub.5                                                                            CH.sub.2 COOCH.sub.3                                                                       "          624                 130                                                                               "  "         "       "           C.sub.2 H.sub.4 OH                                                                         "          645                 131                                                                               "  "         "       C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          626                 132                                                                               "  "         "       C.sub.2 H.sub.5                                                                             ##STR19##  "          641                 133                                                                               "  "         "       "                                                                                           ##STR20##  "          638                 134                                                                               "  "         "       "           C.sub.2 H.sub.4 OCH.sub.3                                                                  "          642                 135                                                                               "  "         "       "           C.sub.2 H.sub.4 OC.sub.2 H.sub.4                                               OCH.sub.3   "          642                 136                                                                               "  COOCH.sub.3                                                                              "       "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          618                 137                                                                               "  COOC.sub.2 H.sub.5                                                                       "       "           "           "          618                 138                                                                               "  CN        CH.sub.3                                                                               "           C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          649                 139                                                                               "  "         "       C.sub.2 H.sub.4 CN                                                                         "           "          627                 140                                                                               "  "         "       C.sub.2 H.sub.4 OCOOCH.sub.3                                                               C.sub.2 H.sub.4 OCOOCH.sub.3                                                               "          630                 141                                                                               "  "         "       C.sub.2 H.sub.4 COOCH.sub.3                                                                C.sub.2 H.sub.4 COOCH.sub.3                                                                "          631                 142                                                                               "  "         NHCOCH.sub.3                                                                           C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                            "          656                 143                                                                               "  "         "       C.sub.2 H.sub.4 OCH.sub.3                                                                  C.sub.2 H.sub.4 OCH.sub.3                                                                  "          652                 144                                                                               "  "         Cl      C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                "          620                 145                                                                               "  COOCH.sub.3                                                                              CH.sub.3                                                                               C.sub.2 H.sub.5                                                                            "           "          613                 146                                                                               "  "         "       C.sub.2 H.sub.4 CN                                                                         C.sub.2 H.sub.5                                                                            "          608                 147                                                                               "  "         Br      C.sub.2 H.sub.4 OCOCH.sub.3                                                                C.sub.2 H.sub.4 OCOCH.sub.3                                                                Blue       615                 __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR21##                                                                                                                               λ max                                                         Dyeing Shade                                                                             (acetone)            No.                                                                               X  Y     Z      R.sup.1    R.sup.2       R.sup.3                                                                            (on polyester                                                                            nmbers)              __________________________________________________________________________     148                                                                               H  COOCH.sub.3                                                                          H      C.sub.2 H.sub.4 CN                                                                        CH.sub.2CHCH.sub.2                                                                           CH.sub.3                                                                           Brilliant                                                                                603e                 149                                                                               "  CN    "      C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.4 COOCH.sub.3                                                                  "   "         626                  150                                                                               "  "     "      "          CH.sub.2 COOCH.sub.3                                                                         "   "         613                  151                                                                               "  "     "      H          C.sub.2 H.sub.4 COOCH.sub.3                                                                  "   "         605                  152                                                                               "  "     "      "          C.sub.2 H.sub.4 COOC.sub.2 H.sub.4 OCH.sub.3                                   3             "   "         605                  153                                                                               "  "     "      C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                                  "   "         614                  154                                                                               "  "     "      C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.4 OH                                                                           "   "         637                  155                                                                               "  "     "      H                                                                                          ##STR22##    "   "         609                  156                                                                               "  "     "      "          C.sub.2 H.sub.4 OCH.sub.3                                                                    "   "         621                  157                                                                               "  "     CH.sub.3                                                                              C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.4 OCOCH.sub.3                                                                  "   "         639                  158                                                                               "  "     "      "          "             Cl  "         602                  159                                                                               "  "     H      "          C.sub.2 H.sub.4 COOCH.sub.3                                                                  "   "         601                  160                                                                               "  "     "      C.sub.2 H.sub.4 OH                                                                        H             "   "         621                  161                                                                               "  "     "      C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                                  "   "         592                  162                                                                               "  "     NHCOCH.sub.3                                                                          C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                              CH.sub.3                                                                           "         648                  163                                                                               "  "     H      C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                                  OCH.sub.3                                                                          "         624                  164                                                                               "  "     "      C.sub.2 H.sub.4 COOCH.sub.3                                                               H             "   "         613                  165                                                                               "  "     "      C.sub.2 H.sub.4 CN                                                                        C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                          "   "         607                  166                                                                               "  COOC.sub.2 H.sub.5                                                                   "      C.sub.2 H.sub.4 COOCH.sub.3                                                               H             CH.sub.3                                                                           "         601                  167                                                                               "  "     "      C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                                  "   "         612                  168                                                                               Cl CN    "      "          "             "   "         624                  169                                                                               "  "     "      C.sub.2 H.sub.4 COOCH.sub.3                                                               H             "   "         613                  170                                                                               "  "     NHCOCH.sub.3                                                                          C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                              "   "         659                  171                                                                               "  "     NHSO.sub.2 CH.sub.3                                                                   "          "             Cl  "         646                  172                                                                               NO.sub.2                                                                          "     H      "          C.sub.2 H.sub.4 OCOCH.sub.3                                                                  CH.sub.3                                                                           "         643                  173                                                                               "  "     CH.sub.3                                                                              "          "             OCH.sub.3                                                                          "         657                  174                                                                               CF.sub.3                                                                          "     Cl     C.sub.2 H.sub.4 OCOCH.sub.3                                                               "             CH.sub.3                                                                           "         623                  175                                                                               "  "     H      C.sub.2 H.sub.4 OC.sub.2 H.sub.4 OCH.sub.3                                                H             "   "         607                  176                                                                               H  "     "      C.sub.2 H.sub.4 CN                                                                        C.sub.2 H.sub.5                                                                              "   "         605                  __________________________________________________________________________

REFERENCE EXAMPLE 1

The dyestuffs of the present invention and the known dyestuff (dyestuff described in Japanese Patent Application (OPI) No. 47680/74) were examined in order to measure pollution of the white texture in printing and white dischargeability in alkali resist- and discharge printing.

(a) Pollution of white texture:

A woven fabric of polyester fibers was printed with using dyestuffs shown in the following Table 3 according to the process described in Example 2, and the degree of pollution on non-dyeing parts (white texture) caused by the non-setting dyestuff was determined by a gray scale (indication of 5 grades).

(b) White dischargeability in alkali resist- and discharge printing:

A woven fabric of polyester fibers was printed with using dyestuffs shown in the following Table 3 according to the process described in Example 3, and the white part was determined by a gray scale (indication of 5 grades).

Grade 5 is the best value in both cases of pollution of white texture and white dischargeability. The dyestuff which shows values nearer grade 5 has a high commercial value, because the pollution of white texture is less caused and the white dischargeability is better.

                                      TABLE 3                                      __________________________________________________________________________      ##STR23##                                                                                                            Pollution of                                                                          White dischargeability                                                  white texture                                                                         in alkali resist- and                   X  Y     Z      R.sup.1 R.sup.2 (grade)                                                                               discharge                        __________________________________________________________________________                                                   printing                         Dyestuff for                                                                          H  CN    H      C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 CN                                                                     1      1                                comparison                                                                     Dyestuff of                                                                    this invention                                                                 1      H  CN    H      C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 COOCH.sub.3                                                            4      4                                2      "  COOCH.sub.3                                                                          "        "     C.sub.2 H.sub.4 CN                                                                     4      4                                3      "  CN    "      C.sub.2 H.sub.4 OCOCH.sub.3                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                            3      3                                4      "  "     "      C.sub.2 H.sub.4 COOCH.sub.3                                                            C.sub.2 H.sub.4 COOCH.sub.3                                                            4-5    4-5                              5      CF.sub.3                                                                          "     "      C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.4 COOCH.sub.3                                                            3      3                                6      Cl "     "      C.sub.2 H.sub.4 OCOCH.sub.3                                                            C.sub.2 H.sub.4 OCOCH.sub.3                                                            3      3                                7      H  CN    NHCOCH.sub.3                                                                          C.sub.2 H.sub.5                                                                        C.sub.2 H.sub.5                                                                        2-3    2-3                              8      "  "     NHSO.sub.2 CH.sub.3                                                                   C.sub.2 H.sub.4 OCH.sub.3                                                              C.sub.2 H.sub.4 OCH.sub.3                                                              2-3    2-3                              __________________________________________________________________________

REFERENCE EXAMPLE 2

The dyestuffs of the present invention and the known dyestuffs (dyestuffs described in Japanese Patent Application (OPI) No. 41734/76) were examined in order to measure temperature dependence. The temperature dependence was measured by the following method.

Dyeing was carried out under dyeing conditions of 130° C.×60 minutes and 120° C.×60 minutes according to the process described in Example 1. The dyeing densities of each dyeing fabric were measured by eyes, and the temperature dependence was determined according to the following formula: ##EQU1## (The temperature for dyeing is generally 130° C., and the dyeing density reduces with falling of the temperature. The excellent dyestuff is that which causes less reduction of the dyeing density, and the most excellent dyestuff is that wherein the value of temperature dependence determined by the above-described formula is 100.)

REFERENCE EXAMPLE 2-1

    ______________________________________                                          ##STR24##                                                                                            Temperature                                                        D           dependence                                              ______________________________________                                         Dyestuff of this invention                                                                   ##STR25##    90                                                  Dyestuff for comparison                                                                      ##STR26##    40                                                  ______________________________________                                    

REFERENCE EXAMPLE 2-2

    ______________________________________                                          ##STR27##                                                                                            Temperature                                                        D           dependence                                              ______________________________________                                         Dyestuff of this invention                                                                   ##STR28##    90                                                  Dyestuff for comparison                                                                      ##STR29##    40                                                  ______________________________________                                          REFERENCE EXAMPLE 2-3

    ______________________________________                                          ##STR30##                                                                                           Temperature                                                         D          dependence                                               ______________________________________                                         Dyestuff of this invention                                                                   ##STR31##   80                                                   Dyestuff for comparison                                                                      ##STR32##   40                                                   ______________________________________                                    

REFERENCE EXAMPLE 2-4

    ______________________________________                                          ##STR33##                                                                                            Temperature                                                        D           dependence                                              ______________________________________                                         Dyestuff of this invention                                                                   ##STR34##    90                                                  Dyestuff for comparison                                                                      ##STR35##    30                                                  ______________________________________                                    

REFERENCE EXAMPLE 2-5

    ______________________________________                                          ##STR36##                                                                                               Temperature                                                  D                 dependence                                           ______________________________________                                         Dyestuff of this invention                                                                ##STR37##          85                                               Dyestuff for comparison                                                                   ##STR38##          40                                               ______________________________________                                    

REFERENCE EXAMPLE 2-6

    ______________________________________                                          ##STR39##                                                                                             Temperature                                                      D             dependence                                             ______________________________________                                         Dyestuff of this invention                                                                  ##STR40##      90                                                 Dyestuff for comparison                                                                     ##STR41##      40                                                 ______________________________________                                     

What is claimed is:
 1. Disazo dyestuff for polyester fibers represented by the following formula: ##STR42## wherein X represents hydrogen, Y represents cyano, Z represents hydrogen, R¹ represents lower alkyl, cyanoalkyl, hydroxyalkyl, lower alkoxyalkyl, lower alkoxyalkoxyalkyl, aryloxyalkyl, acyloxyalkyl, alkenyloxyalkyl, lower alkoxycarbonylalkyl, lower alkoxyalkoxycarbonylalkyl, or lower alkoxycarbonyloxyalkyl, R² represents hydroxyalkyl, lower alkoxyalkyl, lower alkoxyalkoxyalkyl, aryloxyalkyl, acyloxyalkyl, alkenyloxyalkyl, lower alkoxycarbonylalkyl, lower alkoxyalkoxycarbonylalkyl, or lower alkoxycarbonyloxyalkyl, and R³ represents hydrogen, methyl, chlorine or methoxy, but R² represents lower alkyl in case that R³ represents methyl. 